4H-1-Benzopyran-4-one, 2,3-dihydro-7-hydroxy-2-(4-hydroxyphenyl)-

Details

• Internal ID: df30637d-4d82-4578-ae64-513fa737e07b
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Flavanones
• IUPAC Name: 7-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
• SMILES (Canonical): C1C(OC2=C(C1=O)C=CC(=C2)O)C3=CC=C(C=C3)O
• SMILES (Isomeric): C1C(OC2=C(C1=O)C=CC(=C2)O)C3=CC=C(C=C3)O
• InChI: InChI=1S/C15H12O4/c16-10-3-1-9(2-4-10)14-8-13(18)12-6-5-11(17)7-15(12)19-14/h1-7,14,16-17H,8H2
• InChI Key: FURUXTVZLHCCNA-UHFFFAOYSA-N
• Popularity: 744 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₂O₄
• Molecular Weight: 256.25 g/mol
• Exact Mass: 256.07355886 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.80
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• 69097-97-8
• (+/-)-Liquiritigenin
• 41680-09-5
• 4H-1-Benzopyran-4-one, 2,3-dihydro-7-hydroxy-2-(4-hydroxyphenyl)-
• 7-hydroxy-2-(4-hydroxyphenyl)chroman-4-one
• CHEMBL271939
• ( inverted exclamation markA)-Liquiritigenin
• 7-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
• 7-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one
• 7,4'-Dihydroxyflavanone
• ()-Dihydrodaidzein
• Liquiritin rhamnoside
• (R/S)-Liquiritigenin
• 7,4''-dihydroxyflavanone
• 4'',7-Dihydroxyflavanone
• cid_1889
• Oprea1_134668
• MLS000697612
• SCHEMBL1071066
• HY-N0377A
• DTXSID90274339
• DTXSID90961898
• CHEBI:136678
• FURUXTVZLHCCNA-UHFFFAOYSA-N
• HMS2268K07
• HMS3604C10
• BDBM50228333
• MFCD00017478
• MFCD00287289
• AKOS024462907
• CCG-103352
• NCGC00247525-01
• SMR000470946
• SY076300
• CS-0145110
• FT-0627876
• FT-0777980
• 7-Hydroxy-2-(4''-hydroxyphenyl)chroman-4-one
• B0005-464393
• 7-Hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one #
• 7-hydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9881	98.81%
Caco-2	-	0.7591	75.91%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.8241	82.41%
OATP2B1 inhibitior	-	0.6348	63.48%
OATP1B1 inhibitior	+	0.8593	85.93%
OATP1B3 inhibitior	+	0.9756	97.56%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8490	84.90%
P-glycoprotein inhibitior	-	0.9166	91.66%
P-glycoprotein substrate	-	0.9037	90.37%
CYP3A4 substrate	-	0.5451	54.51%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.3531	35.31%
CYP3A4 inhibition	+	0.5207	52.07%
CYP2C9 inhibition	+	0.9352	93.52%
CYP2C19 inhibition	+	0.8456	84.56%
CYP2D6 inhibition	-	0.8850	88.50%
CYP1A2 inhibition	+	0.8739	87.39%
CYP2C8 inhibition	-	0.7465	74.65%
CYP inhibitory promiscuity	+	0.5609	56.09%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9513	95.13%
Carcinogenicity (trinary)	Non-required	0.5441	54.41%
Eye corrosion	-	0.9883	98.83%
Eye irritation	+	0.9549	95.49%
Skin irritation	+	0.5175	51.75%
Skin corrosion	-	0.9852	98.52%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8366	83.66%
Micronuclear	+	0.8559	85.59%
Hepatotoxicity	-	0.6500	65.00%
skin sensitisation	-	0.8864	88.64%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	+	0.5378	53.78%
Acute Oral Toxicity (c)	II	0.4621	46.21%
Estrogen receptor binding	+	0.6034	60.34%
Androgen receptor binding	+	0.6289	62.89%
Thyroid receptor binding	+	0.6747	67.47%
Glucocorticoid receptor binding	+	0.7422	74.22%
Aromatase binding	+	0.6927	69.27%
PPAR gamma	+	0.7624	76.24%
Honey bee toxicity	-	0.8576	85.76%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.8043	80.43%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1978	P11511	Cytochrome P450 19A1	340 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.30%	91.11%
CHEMBL2581	P07339	Cathepsin D	92.90%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.71%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.13%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.76%	89.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.03%	90.71%
CHEMBL242	Q92731	Estrogen receptor beta	86.62%	98.35%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.02%	96.09%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	84.42%	85.11%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	84.41%	90.93%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	83.24%	93.40%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.25%	99.23%
CHEMBL236	P41143	Delta opioid receptor	80.80%	99.35%
CHEMBL4630	O14757	Serine/threonine-protein kinase Chk1	80.39%	97.03%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	80.36%	85.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.11%	86.33%

Plants that contains it

• Astragalus microcephalus
• Brosimum acutifolium
• Butea monosperma
• Clausena excavata
• Crinum bulbispermum
• Dalbergia louvelii
• Dalbergia odorifera
• Dalbergia parviflora
• Dracaena draco
• Erythrina fusca
• Flemingia macrophylla
• Glycyrrhiza glabra
• Glycyrrhiza inflata
• Glycyrrhiza pallidiflora
• Glycyrrhiza uralensis
• Hedysarum polybotrys
• Lespedeza cyrtobotrya
• Maackia amurensis
• Oxytropis falcata
• Oxytropis trichophysa
• Pancratium maritimum
• Platymiscium floribundum
• Pterocarpus santalinus
• Sinofranchetia chinensis
• Sophora koreensis
• Spatholobus suberectus
• Umtiza listeriana

Cross-Links

• PubChem: 1889
• LOTUS: LTS0155090
• wikiData: Q72487544